Note: This is a re-write of Babysitting Amanda 1 and 2. I cannot plagiarize my own stories so do not accuse me of such. As usual, do not waste time with accusations and insults against me. Finally, some ages and details have been changed from the original stories. If you have not read my stories before, make sure you read My Cousin Tom 1 and 2.
Let me introduce myself. My name Jake and I am 16 years old. I was your classic horny teenage guy. My hair is dark black, which goes well with my brown eyes. I've always been slightly fit, never working out yet somehow keeping myself in shape through basic exercise. I've never managed to have a steady girlfriend, so often I fantasized to thoughts of the busty girls from around my school. All that changed when I met Amanda. After my experiences with her, images of her sexy, then 14 year old body filled my mind every time I masturbated. I must have cum literally gallons in the months after we meet, always looking forward to a time when we would see each other again.
Every night after my first experience with Amanda, I found myself jacking off to memories of her. She was the first person I had ever done anything sexual with, and I was desperate to see her again and allow things between us to continue. The opportunity came during a phone call from Amanda's mother. She had found herself in need of a babysitter one day, and Amanda mentioned me. She got my phone number from Tom's parents and asked me to baby-sit both Amanda and her younger sister, Becky, who was seven. As soon as she mentioned Amanda's name, I was on board with the idea and canceled all other plans for that day. I would again be needed overnight- from 10 am Monday to 6:30 pm Tuesday. It turns out that her mom was attending a business meeting until late and would sleep in her office, while I stayed overnight. Not that I was complaining.
At exactly 9:55 am Monday I got to their house, just down the street from Tom's. I knocked, and Amanda's mom, Jane, soon answered. She was a plain, brown haired woman with a nice body. She quickly ushered me in and briefed me. The girls were allowed to go to the playground, but could not leave my sight. They could have friends over- however many I was comfortable with in the yard but only two inside. Both girls were to bath that night, but Amanda could take a shower while Becky took a bath. Considering the fact that I was a guy, she said that Becky would be more comfortable if Amanda bathed her. "No problem" I said. "I understand". After giving me a list of emergency numbers, she left me there and went to her bedroom to wash up.
Amanda, who had been watching the whole exchange, seemed to float over into my arms. She snuggled her head onto my shoulder and said "I'm so glad you're here, our old babysitter wasn't nearly so hot." Smiling, I turned to her and whispered "I think about you every night, I'm so glad to see you again." She smiled a gesture that warmed the very depths of my heart and existence. I kissed her then, a soft but passionate kiss on her soft lips. We held each other for a few more seconds, but broke apart at the sound of footsteps. Becky walked in. Like her mother, she had shoulder length brown hair. Her eyes were a soft blue, and she wore a baggy T-shirt over a pair of hand-me-down blue jeans. Seeing me, she drew back slightly. "Its ok Becky", Amanda said with a helpful-big-sister sort of smile. "Jake here is cool". I gave Becky a small, friendly smile, and was glad when she smiled back. Amanda's mom reappeared, and after addressing her daughters and wishing us a good night, turned out the door and left.
As I heard her car pull away, I asked Amanda what the girls normally did at that time. She suggested the playground, and I agreed. Becky had to change into a tighter shirt that wouldn't flop down on her easily, and we were off. At the playground, several of the neighborhood boys recognized me from Tom’s and waved. I kept a close eye on Becky the entire time, while Amanda went over to her own friends. I recognized Jessica and Katy and waved. Giggling, they waved back and returned to their activities. Becky climbed up onto a squat pair of monkey bars, and I stayed nearby in case she fell. After climbing across once, she began to horse around on the bars, pulling herself up on top. Locking her legs tight around the bar, she let her chest fall down towards the ground until she was hanging upside down. She looked silly for a moment, until her shirt billowed down and covered her face. She wore nothing underneath it, and her young, flat chest was exposed to the world. My eyes were drawn to the two tiny mounds that were her breasts. I scrambled over and picked her up. She let go off the bars and proceeded to pout as I set her down. I told her: "You can climb up again, but you'll have to tuck your shirt in first". I demonstrated how, and she did so before climbing back up into the same position. Becky played on the bars until about 12, when I decided it was time for lunch and a nap. Gathering Amanda from her gaggle of friends and a disappointed Becky from the monkey bars, I took them both home and fixed sandwiches. Afterwards I had to put Becky to bed. Needless to say she did not go quietly.
After wrestling her into the bed and threatening to spank her if she got out, she gave up. I stayed nearby with my eye on her until she was completely asleep, and then went to the living room with Amanda. I barely got into the room before we were in each others arm, making out blissfully. We fell onto the couch and she ended up on top of me, her gentle weight pressing on my body. I found myself in heaven all over again. Her hands pried my shirt off and traveled over my chest, stroking my abs. My hands traveled her back, up and down and side to side. I brought them around her shirt and up the front. I rubbed her stomach though her shirt then slid my hands underneath. My handles traveled up her chest and to her bra. Reaching underneath it, I tweaked her nipples softly, which elicited a soft moan from her. I squeezed each of them softly, then pulled my hands of and embraced her again. She was disappointed. I kissed her on the lips. "Not when your sister might walk in" I whispered lovingly. She gave a mischievous smile but relented. I pulled my shirt back on and we kissed for some time, until she fell asleep there on my chest. I kept myself awake, listening to her breathing and feeling the steady rise and fall of her stomach. She stirred around 2 o’clock, and I woke her up with a kiss and a smile. She got up and left for the bathroom to do what teenage girls do.
I went to Becky's room and gently roused her from her sleep. She grumbled slightly, and I had to help her out of bed. She was soon the little firecracker, however, and I took her into the back yard to play. I took a seat in a lawn chair and Amanda sat next to me. Some neighborhood kids came over, and they played like wild animals for the next few hours. At around 6, it started getting dark. Gathering up all the kids, I took them all home. Becky held onto my arm the entire time, which surprised me. She was really warming up to me rather quickly, which I didn't expect. We dropped them all off and began to head back. I was now carrying Becky while Amanda held tightly onto my arm. At the house, they settled into watching cartoons. Becky and Amanda were on either side of me, both leaning against me, although Amanda had her arm around me. Becky nuzzled up closer, and I began to see just how like her sister she was becoming. At 8 pm, I told them to get dressed for bed. They disappeared to their rooms briefly. Amanda came back, barely dressed at all. She wore an XXL T-Shirt. She bent over to pick up the remote, and I was greeted with a magnificent view of her tight young ass. Becky was similarly dressed.
I gave them permission to watch what they wanted. They started bickering and were soon physically fighting over what to watch. It was a sight to see, two beautiful young girls wrestling on the floor with no thought towards modesty. Both of their panties were exposed to me several times, and I was even granted a good look at Amanda's pert young breasts. Soon, however, hair was pulled and nails came out. Amanda gave Becky a scratch and Becky pulled out some of Amanda's hair. I broke it up and set them both on opposite sides of the room. "You're sisters" I said. "Learn to get along". They proceeded to continue bickering, arguing loudly and driving me insane. I had enough. Their mother had given me permission to spank them, and I pulled Amanda over my knee first. Her shirt flopped down over her head, revealing her panty-clad backside to me. I gave it 10 firm smacks, leaving her ass beet-red. (sorry for the pun). I let her go, saying "Do what you want, but if I were you I wouldn't sit down for a while." I pulled Becky over next and gave her the same treatment. I hit her carefully, leaving her small butt pink. I set her free with the same warning. Amanda wandered off to her room. When she reappeared, lifting her skirt to show she was wearing a tiny string thong, sparing the pressure of panties on her sore bottom. Becky complained. "Hey, you know I don't have any of those!" I smacked my hands loudly as a warning, and they both shut up. I took Amanda to her room and made her change back into normal panties. I took them both back to the living room and made them apologize to each other.
Next, it was bath time. As a final punishment, I made Amanda share the bath with Becky. I was about to leave when Becky spoke up. "Aren't you going to wash us?" "I figured you would be more comfortable with Amanda, she can do it." "No, you do it. Please". I now had two gorgeous young girls in completely naked front of me, and now one of them wanted me to run my hands all over her! I couldn't refuse. Grabbing a wash cloth, I started on Becky's back. Amanda gave me a sly grin and wink and settled against the wall of the bath tub. I washed Becky's legs, down to her feet, which I massaged carefully. I switched to her stomach, skipping over her pussy and breast area. The whole time my eyes were fixed on her tiny young pussy. I finished her arms and was about to leave her when she again stopped me. "You're supposed to wash ALL of me". My mouth dropped. "But those are your privates, you can do them". Her response shocked me. "But I WANT you to do them". I didn't protest. Starting with her feet, I slowly brought the washcloth up her legs to her small, warm snatch. I washed the edges first, and then concentrated on her soft young hole. She moaned quietly, enjoying it. I got more brazen, hooking my finger in slightly and massaging her clit. She gasped and fell back against the wall of the tub. I stopped then- to her obvious disappointment- and started on her chest. I massaged each of her nipples and ran the cloth over her flat chest. I heard her breath quicken again and again stopped, leaving her obviously disappointed. I was beginning to see through her initial innocence and learn just how horny this young girl was. I then offered the rag to Amanda, who refused. "You did her, now you have to do me!" she insisted. Shrugging, I agreed. I was far less apprehensive about Amanda and my finger was soon deep cleaning her pussy to her audible gasps and moans. I looked up for a second and saw Becky's hand below the water, seemingly in her crotch, her eyes looking on with fascination. I rubbed Amanda's breasts softly. She was now gasping in my hands, barreling towards an orgasm. I stopped suddenly and she gave a sigh of disappointment. I got towels down and told them to get out.
Becky dragged her dripping wet body out first and insisted I dry her. I ran the towel down her arms, then knelt as I carefully dried each leg. She turned, and her pussy was level with my face. I sniffed deeply, inhaling her scent, before carefully drying over her pussy and chest. Amanda was already out and dry. Both girls wore T-shirts but nothing else. The veil of innocence was gone, and I knew they would both want more.
We returned to the couch. Becky cut to the chase and sat on my lap. She pulled her shirt up so that her naked pussy rested on top of my crouch. I slipped on hand around her and cupped her entire crotch. Amanda sat beside us. I now realized that this whole night they had been setting me up for the bath, and that I had fallen into their trap completely. Not that I was complaining! I began to finger Becky openly, leaving her gasping in my arms. I was careful, only letting the first digit of my finger disappear into her sweet little snatch. Amanda stood up and pulled her hot little sister off me. "All we have is shirts on. You can at least return the favor" she demanded. I stood up, and the girls stripped my shirt, pants, and even socks off. Finally, Becky reached for my boxers. She tugged then down gently, and my dick popped out, bopping her on the nose. She was fascinated with it. "I've never seen one before!" she said, awed. She pulled it down and laughed when it sprung back up. Amanda stepped in and held it in her hands. The sight of two girls playing with my cock almost made me cum right away, but I held it. Amanda began to jerk me off, and I fell back into the couch. Her hand traveled up and down, and I moaned loudly. Both girls tugged their shirts off and were naked. Becky climbed up onto the couch and kissed me; no little girl kiss but a fully adult. I pushed my tongue into her mouth and she entered mine. She tasted sweet, like sugar. I pulled her face to mine and kissed her hard. Amanda stopped, and the two switched places. Becky was inexperienced but had learned from her sister. I felt her small hands travel the length of my 6 1/2 inch member, struggling to wrap her fingers around my girth. Amanda stopped making out with me long enough to tell her sister how to suck me. My eyes were riveted as my cock disappeared into Becky's small mouth. Her lips seemed apprehensive at first and slid around my head, then down. More confident, her tongue joined the picture and licked up and down my shaft. Amanda buried her mouth and I found myself in heaven all over again. We all became more and more passionate, until Amanda stopped- just before I orgasmed.
She led us to her room and cleaned the sheets off her bed. Before things went any further, I asked Amanda just how far they both wanted to go. "Jake, I love you. I want you to take my cherry tonight. Make me a virgin no more!" Becky agreed. I agreed. Becky was to be first. She came over to me. I pulled her tight young pussy to my face and gave a tentative lick. I teased her for a while until she began to beg me to eat her out. I felt Amanda take my cock into her mouth and suck, and I leaped into Becky. She gasped as my tongue probed into her, tasting every inch, my mouth sucking for all I was worth. She moaned loudly. I was in bliss and no longer controlled myself. I plunged my tongue deep into her. She went wild. "PLEASE JAKE.......OH YES......OH MY GOD....." I pushed her towards and orgasm. I knew she was close, and thrust my tongue and sucked her all at the same time. With a scream, she orgasmed. Her hot girl cum splashed into my mouth and all over my face. I drank it greedily. I knew she had never felt like this before and was determined to make the feeling last for her. I felt a tingling in my balls and shot my cum into Amanda's waiting mouth. I couldn't see how she took it, but felt suction on my cock head and knew she was gulping every drop. I slowed my pace on Becky, bringing her down bit by bit until she collapsed, exhausted, next to me. "I've never felt that good...............oh my god....." I patted her gently and kissed her, letting her taste herself. She lay quietly by my side, getting her energy back. After a few minutes, she sat up. "Its time" she said, determined. Amanda stroked my cock a few times and Becky walked climbed over to it. I knew that she wanted to lose her cherry now. I stopped them. "Becky, you know this is going to hurt, right?" She nodded. "Are you sure you want this?" "Jake, ever since Amanda first told me about you I wanted you to take my cherry" "Ok, you're can be on top of me here. If it gets too much, just tell me and I'll get you off me." She nodded and sat down on my chest. We prepared to lose our virginities together.
Amanda was off to the side, her finger buried in her pussy. "Save some for me!" I protested. "Don't worry", she said with a wink and a nod to Becky. "I'm ready", Becky said. I grabbed her arms and picked her up, sliding her down to my cock. I kissed her hard, then slipped the head of my cock into her virgin pussy. She was so tight! I realized she was bracing herself, and told her not to. She loosened up, and settled down another inch. I felt skin on my tip and knew it was her hymen. I looked at her one last time, and she nodded. I picked her weight up, then brought her down suddenly. My dick ripped through her hymen, and she screamed in pain and pleasure. I stopped there and laid her on my chest. The pain subsided, and she nodded for me to continue. She moved up and down slowly on my cock, fucking herself. She started to moan as pleasure captured her senses. She got faster and faster. I felt my pole slid in and out of her tight hole, and moaned in approval. She soon became a moaning blur on my cock. Amanda jammed her pussy into my face and I ate her out, moaning and shouting into her pussy. Becky spoke up. "oh yes....fuck me, please.......FUCK ME!!!" she began to shout. I drove my tongue into Amanda, tasting every inch of her as I had Becky. I felt Becky's pussy tighten, and she screamed. "OH MY GOD.....OH MY GOD...............I'M CUUMMMMMMING!!!!" I felt her warm girl cum run down my cock and couldn't hold myself. My balls churned and shot rope after rope of cum into her. Amanda lost it onto my face, and we came together. Amanda's cum slid down the sides of my face, and she screamed in pleasure. Becky slowed down in her fucking, and Amanda fell of me onto the bed. With one last thrust, I pulled Becky off me and laid her down. She was shivering from her orgasm. Amanda bent over and kissed her sister, tasting me from her little sisters mouth. They held each other for some time. We all paused for a while to get our energy back. Afterwards, I knew it would be Amanda's turn.
Amanda and I made sure Becky was comfortable. Her pussy was predictably sore after the hard fucking, and we would work without her. I kissed Amanda and lowered her to my waist. I cast a look at this incredible 14 year old and watched her hover her pussy over my cock. She bent over and sucked her little sister’s juices off, and I moaned as her tongue traveled my shaft. Her pussy was still wet from the tongue lashing I had given her, and she was ready. She lowered herself down, and my cock entered the second virgin pussy that night. Her cunt was a tight fit around my cock, and she slid down an inch. I felt her warm barrier and knew that it would be the second one I claimed that night. I kissed her, and she suddenly seized up and plunged herself down on my cock! I felt her hymen rip and she let out a soft scream. I saw tears in her eyes, but she was determined not to stop. She started to fuck herself gently on my 6 inch dick. I watched and groaned as her pussy traveled up and down my shaft. After about 20 minutes, Becky woke up. She was not happy that we had gone on without her. She kissed me, then moved over to her sister. She bent over and kissed the area where my cock met Amanda's pussy. I felt Amanda's pussy begin to seize up and new she was close to orgasm. I grabbed her sides as she rode my cock like a wild woman, becoming a blur atop my cock. She gave out a scream of orgasmic pleasure, and I felt her pussy juices spill out over my cock. Becky kept up licking, sucking up her sisters cum. I felt the familiar bubbling in my balls and cum erupted from my cock into her pussy. Rope after rope of my cum shoot deep into her, and I felt the mix of our cum running down my cock into Becky's waiting mouth. Amanda drove herself hard, riding out her intense orgasm. She tired, and I helped her off my prick. Both she and Becky collapsed onto the bed next to me. They snuggled up on either side of me, and we fell asleep together. I dreamed that night of the two heavenly young girls that were with me, and of the fun we would have in the future.
After that first night, Amanda's mom asked me to baby-sit more and more often. Soon I was over there several times a week. Amanda, Becky and I fucked constantly while over there, and Amanda and I privately became boyfriend and girlfriend, since she was not much younger than me at all. I cared about her and would have done almost anything she needed or asked.
Amanda came to me one night after the three of us had gone through a particularly thrilling threesome. She told me she was worried about her mom. Her mom, Jane, worked an office job at a market trading firm. Because of her job, Jane was under constant stress. According to Amanda, Jane had not had a boyfriend since soon after Becky was born. Amanda knew her mom masturbated, having spied on her a couple of times. She noticed that poor Jane never got much out of her jilling sessions, and while desperate for male companionship was too worried about her girls to get a boyfriend. Poor Jane, at only 30, was a desperate woman who needed a man to please her badly. Amanda begged for my help. After having slept with Amanda and Becky so many times, I was skilled in getting women off. However, I was uncertain. "You know your mom might not like this idea, I mean I am almost 15 years younger than her". "Becky and I will take care of that" Amanda responded. I was still reluctant. Then Jane nearly ended up in the hospital after a severe stress attack. Out of concern for this family, I agreed to help. The three of us then began to form our plan.
Jane came home one night to find Amanda, Becky and I watching TV. After a brief hello, she went off to take a quick nap. Our plan swung into action. I went to my overnight bag and retrieved some rope, a gag, and a blindfold. The three of us went to Jane's room and slipped in quietly. She was sound asleep. She had already taken off her outer clothing and was left only in her underwear, which made things easy for us. I peeled off her panties while Amanda removed her bra. It was then that I got a good look at Jane for the first time. While I usually didn't care for older women, Jane made my mouth drop open. She was a slender woman, with two small, perfect breasts and a pussy to die for. I shook out of my lust and began to tie her legs to the bed post, while Amanda took care of her arms. Meanwhile, Becky applied the gag and blind fold. I checked the knots on the ropes, making sure they were comfortable yet tight enough to keep Jane from moving to stop us as we worked. I stripped to my boxers while Amanda and Becky went naked. When we were all ready, Amanda went over and gently shook her mom's shoulder.
When Jane awoke, she felt a set of lips on her right breast. I could see the shock on her face through the blindfold and gag. Amanda sucked her mom’s breast, pulling it between her teeth. I felt Jane try to struggle, only to find the bonds far too strong. Becky moved in on her other breast, and soon the two girls were working wonders on Jane, whose apprehension could not withstand the pleasure. I moved in on her pussy. She felt the hot breath on her clit and tried to close her legs, but could not. I touched my tongue to her pussy and she let out an unwilling moan. I went to work on her, having practiced extensively on Becky and Amanda. As my lips propped her outer lips, I felt a shudder travel through her body. I pushed her harder, letting my tongue travel in to lick her inner folds. Jane was soon lost in bliss, well on her way to an orgasm. As she came close to climaxing, I pulled out, patting Amanda and Becky on their sweet young butts. We all stopped, teasing her. I could tell just how badly she now wanted what was coming to her. Amanda went to her mother and removed the blindfold. Jane blinked a few times, then her eyes widened in shock as Amanda leaned over to take her mom's tit into her mouth again. She was now fighting an inner battle between pleasure and decency. Becky and I resumed our places, and she shook in sheer bliss. I knew the battle was almost won. I plunged my tongue deeply into her clit, as Amanda and Becky increased their sucking. Jane was pushed over the edge into in incredible orgasm. Her body shook, out of control, as the orgasm wrecked her. The girls and I pressed on, pushing out every bit of that orgasm. I felt her pussy tense up on her tongue, and felt her cum running down my tongue into my waiting mouth. She had a slightly tart flavor, which I gulped deeply. Not a drop was spilled. With one last thrash and burst of cum, Jane fell still. We pulled away, and Amanda turned to talk to her mother.
"If I take this off, will you yell or scream?" Amanda said, indicating the gag. The submissive look in her mom's eyes gave her the answer. She removed the gag, and her mom breathed deeply. "What the hell is going on?" she said quietly, not daring to yell. She gave me an accusing look. I shrugged my shoulders and indicated Amanda. "It was my idea mom. We've been so worried about you for a long time. We knew how badly you needed sex, and I begged Jake here to help." Amanda said lovingly. Jane was shocked. We told her the whole story, and she was quiet the entire time. The girls kept there hands on her breasts while I massaged her pussy. At the end, she sighed. "I never thought my two little angels.....would be like me." Jane revealed that she had loved the idea of sex at an early age, and had slept with a variety of men. Nothing negative happened until Amanda came along. The dad stayed long enough for Becky, then fled. "I haven't had sex since. It’s been so hard, the reason why is because I love you two too much to risk it." "Its ok mommy, Amanda said: "We WANT to sleep with Jake. If you think he's a good pussy eater, you should feel his dick in you!' Becky laughed in agreement. Jane was apprehensive, but knew she had lost. "Ok, I'll give it a try. But take this crap off of me!" We untied the ropes willingly. Jane flexed herself. "Can I at least go to the restroom?" We relented, but no one bothered putting clothes on.
She went into the restroom, leaving the door open for us to watch. We crowded in for a closer look. As we watched, a golden stream of piss shot from her pussy to the toilet. It was a fascinating sight for someone who had not seen it before. I went over and peed between her legs, our piss mixing before falling into the toilet bowl. When we were done, she allowed me to wipe her pussy and take her back to her room.
Jane laid on her bed. Amanda and Becky moved in first, and soon were both locked on a tit. Jane buried herself in Amanda's sweet young pussy. The sight of this incestrius lesbian threesome hardened my cock instantly. I moved in on Jane's pussy and began to finger her. Her hole was surprisingly tight due to lack of sex in her life. I squeezed two fingers in, and she moaned into Amanda's pussy. I slipped the head of my cock in and slowly moved forward. Jane's pussy gripped my cock tightly as I buried myself up to the hilt. She gasped as the last few inches of my member disappeared into her. When she was ready, I pulled out, then slammed back in. She screamed in pleasure into Amanda's pussy. The vibration sent Amanda crazy, and she shot towards orgasm. Becky's ass ended up in my face, and I fingered her pussy with one hand while holding myself steady with the other. I fucked Jane faster and harder. Her pussy tightened on my cock, sending my pleasure sky high. All the girls were now screaming in pleasure. I moaned as I felt the familiar bubbling in my balls.
Amanda came first, spilling cum all over her moms face. That set Jane off. She thrust herself onto my prick, sending my balls slapping on her ass. I came as well, shooting rope after rope into her. Becky came last, her little girl cum dripping all over my fingers as she screamed in pleasure. We brought each other down from orgasm, as a passionate, moaning foursome. With a wet plop, I eased myself out of Jane and helped Becky get down. Amanda collapsed onto the bed, and we lay there together. Becky and Amanda fell asleep on either side of me. Jane slept behind Amanda. The bed was soaked with cum, but we were too tired to move.
After several hours of sleep Jane and I woke up. We talked for some time. Considering her own craving for sex at her daughter’s age, she understood my position. She agreed to allow Amanda to date me, and that I could come over and fuck her and her girls any time I wanted. She patted my cock and I massaged her pussy as we talked. We fucked again before the girls woke up. I left the considerably happier family, as satisfied man.
Afterwards I came over at least twice a week, enjoying fabulous sex with all three girls. Amanda and I continued dating, but that’s another story. We all kept each other satisfied for a long time.